Hexane → 2-Allyl-4-fluorophenol

HRID 328628Notes

Reaction equation

HRID 328628 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)C=C.[CH3:12][CH2:13][CH2:14]CCC>>[CH2:14]([C:10]1[CH:9]=[C:8]([F:11])[CH:7]=[CH:6][C:5]=1[OH:4])[CH:13]=[CH2:12]

Participants

3

Reactant 2

HCID 8058HexaneHCID 63734213990-72-2

Product 1

HCID 113441122-Allyl-4-fluorophenol

Procedure

381.8 parts of oily 4-allyloxy-fluorobenzene are heated in an oil-bath for 8 hours at a temperature of about 245° -250° C. After cooling, the reaction mixture is poured onto 1200 parts of hexane. The mixture is extracted three times with sodium hydroxide solution 20% (total volume of sodium hydroxide: 2000 parts). The aqueous layer is washed with petroleum ether, acidified with 1300 parts of concentrated hydrochloric acid solution and extracted with ether. The extract is dried over calcium chloride, filtered and evaporated. The oily residue is distilled in vacuo, yielding 313.6 parts of 2-allyl-4-fluorophenol; bp 143° C at 48 mm. pressure; nD20 : 1.5225; d2020 : 1.1130.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted three times with sodium hydroxide solution 20% (total volume of sodium hydroxide: 2000 parts)
  3. washThe aqueous layer is washed with petroleum ether
  4. extractionextracted with ether
  5. dry with materialThe extract is dried over calcium chloride
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-f55a3ce07b2b4eb697710d47253e4d63
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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